Chloroform → HCID 21162716, compound

HRID 894177Notes

Reaction equation

HRID 894177 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[C:13]([CH:16]([CH3:18])[CH3:17])[CH:14]=[CH:15][C:8]=3[C:7](=[O:19])[C:6]=2[CH:20]=1.[CH3:21][N:22](C)C=O.C(Cl)(Cl)Cl.[C-]#N.[Na+]>O>[CH:16]([C:13]1[CH:14]=[CH:15][C:8]2[C:7](=[O:19])[C:6]3[CH:20]=[C:2]([C:21]#[N:22])[CH:3]=[CH:4][C:5]=3[CH2:11][O:10][C:9]=2[CH:12]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 21162725HCID 21162725, compound

Product 1

HCID 21162716HCID 21162716, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a mixture of 8.39 gm. (0.0253 mole) of 9-bromo-6,11-dihydro-3-isopropyl-11-oxodibenz[b,e]oxepin, 4.83 gm. (0.0539 mole) of cuprous cyanide and 30 ml. of dimethylformamide for 8 hours with vigorous stirring. Cool the reaction mixture and shake with a mixture of 36 ml. of chloroform, 25 ml. of saturated sodium cyanide solution and 25 ml. of water until all solids have dissolved. Separate the organic layer, wash with aqueous sodium cyanide solution and water and dry over anhydrous magnesium sulfate. Remove the solvent under vacuum. Purity the resulting oil (7.01 gm.) by column chromatography on silica gel with benzene as eluant to obtain the title product [yield 2.8 gm., m.p. 101°-108° C., showing a single spot, Rf =0.18 on thin layer chromatography or silica gel with benzene as the solvent system, pmr (CDCl3 1,23(6H, d, (CH3)2CH--), 2.95 (1H,m, (CH3)2CH--), 5.20 (2H,s, CH2O)].

Workup

  1. temperatureReflux
  2. additiona mixture of 8.39 gm
  3. temperatureCool the reaction mixture and shake
  4. additionwith a mixture of 36 ml
  5. customSeparate the organic layer
  6. washwash with aqueous sodium cyanide solution and water
  7. dry with materialdry over anhydrous magnesium sulfate
  8. customRemove the solvent under vacuum

Sources & evidence

ORD record
ord-595028f06d8646ffa2e51e13c21173e5
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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